Pesticidal composition for seed treatment

ABSTRACT

The present invention provides an at least quaternary composition for controlling insects or representatives of the order Acarina and microorganisms, which composition comprises: (A) an insecticidally effective amount of at least one neonicotinoid or phenylpyrazole insecticide, and (B) a fungicidally effective amount of at least three fungicides including: (B1) at least one phenylamide (acylalanine type), (B2) at least one phenylpyrrole and (B3) at least one triazole.

FIELD OF THE INVENTION

[0001] The present invention relates to an at least quaternarypesticidal composition that is suitable for controlling insects and/orrepresentatives of the order Acarina and microorganisms, especiallyphytopathogenic fungi, comprising (a) at least one insecticide and (b)at least three fungicides. The pesticidal composition is particularlysuitable for the protection of plant propagation materials.

BACKGROUND OF THE INVENTION

[0002] Certain mixtures of active ingredients for controlling pests aredescribed in the literature. The biological properties of those knownmixtures are not entirely satisfactory in the area of pest control,toxicity, pest resistance and loading rates. The protection of plantpropagation materials (seed treatments) with pesticides are targetapplications which partially address the need for a reduction ofenvironmental and worker exposure and pest resistance buildup when usedalone or in conjunction with foliar or furrow pesticide applications.However, there is also a need to make available other mixtures whichreduce the need for older acutely toxic insecticides and to reduceloading rates. Among the older insecticides, the following may bementioned: tefluthrin, terbufos, cypermethrin, thiodicarb, lindane,furathiocarb, acephate, butocarboxim, carbofuran, NTN, endosulfan,diethion, aldoxycarb, methiocarb, oftanol, (isofenphos), chlorpyrifos,bendiocarb, benfuracarb, oxamyl, parathion, capfos, dimethoate, fonofos,chlorfenvinphos, cartap, fenthion, fenitrothion, HCH, deltamethrin,malathion, disulfoton. Accordingly, there is a need to provide pesticidecompositions and methods for the protection of plant propagationmaterials, especially those compositions having improved biologicalproperties, for example synergistic pesticidal properties, especiallyfor controlling insects and representatives of the order Acarina andmicroorganisms. That problem is solved according to the invention by theprovision of the present at least quaternary pesticidal composition.

SUMMARY OF THE INVENTION

[0003] The present invention provides an at least quaternary compositionfor controlling insects or representatives of the order Acarina andmicroorganisms, which composition comprises: (A) at least oneinsecticidally or acaricidally active compound, and (B) at least threefungicidally active compounds.

[0004] More specifically, the present invention provides an at leastquaternary composition for controlling insects or representatives of theorder Acarina and microorganisms, especially phytopathogenic fungi, thatis particularly suitable for the protection of plant propagationmaterials such as crop seeds; including oil seeds (especially canola(rape) seed). The at least quaternary pesticidal composition of thepresent invention comprises: (A) an insecticidally effective amount ofat least one neonicotinoid or phenylpyrazole insecticide, and (B) afungicidally effective amount of at least three fungicides including:(B1) at least one phenylamide (acylalanine type), (B2) at least onephenylpyrrole and (B3) at least one triazole.

[0005] The invention also relates to a process for protecting the plantpropagation materials and the plants resulting therefrom against insectsand fungal diseases using a pesticidal composition according to theinvention. It also relates to the said plant propagation materialscoated with the said pesticidal composition.

[0006] The present invention makes it possible to dress or treat seedsand other plant propagation materials with lower amounts of olderacutely toxic biocides than is known from the prior art and, in mostcases, replaces such older acutely toxic biocides; the inventiontherefore represents a material enrichment of the art.

DESCRIPTION OF SPECIFIC EMBODIMENTS Insecticide Component (A)

[0007] Preferred are at least quaternary pesticidal compositionscomprising as insecticidally active ingredient (A):

[0008] at least one neonicotinoid compound of formula (I)

[0009] wherein

[0010] A is 2-chloropyrid-5-yl, 2-methylpyrid-5-yl, 1-oxido-3-pyridinio,2-chloro-1-oxido-5-pyridinio, 2,3-dichloro-1-oxido-5-pyridinio,tetrahydrofuran-3-yl, 5-methyl-tetrahydrofuran-3-yl or2-chlorothiazol-5-yl group,

[0011] R is hydrogen, C₁-C₆alkyl, phenyl-C₁-C₄alkyl, C₃-C₆cycloalkyl,C₂-C₆alkenyl or C₂-C₆alkynyl;

[0012] R₁ and R₂ are independently of each other C₁-C₄-alkyl,C₁-C₄-alkenyl, C₁-C₄-alkinyl,

[0013] —C(═O)—CH₃ or benzyl; or together form a group —CH₂—CH₂—,—CH₂—CH₂—CH₂—, —CH₂—O—CH₂—, —CH₂—S—CH₂—, —CH₂—NH—CH₂— or—CH₂—N(CH₃)—CH₂—; and

[0014] X is N—NO₂ or N—CN or CH—NO₂;, or, where appropriate, a tautomerthereof, in each case in free from or in salt form; or

[0015] at least one phenylpyrazole compound of formula (II)

[0016] wherein

[0017] R₁ and R₂ may represent a hydrogen or halogen atom (at least oneof them is preferably other than hydrogen),

[0018] R₃ may represent a halogen atom or a haloalkyl or haloalkoxy orSF₅ group, in the 4 position on the phenyl ring,

[0019] R₄ may represent an alkyl or haloalkyl group,

[0020] R₅ may represent an amino group which may be mono- or di-substituted by an alkyl or haloalkyl radical, acyl, alkoxycarbonyl, and

[0021] n is 0, 1 or 2; in free from or in salt form.

[0022] The compounds (I) may be in the form of tautomers. Accordingly,hereinbefore and hereinafter, where appropriate the compound compounds(I) are to be understood to include corresponding tautomers, even if thelatter are not specifically mentioned in each case.

[0023] The compounds (I) to (II) are capable of forming acid additionsalts. Those salts are formed, for example, with strong inorganic acids,such as mineral acids, for example perchloric acid, sulfuric acid,nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, withstrong organic carboxylic acids, such as unsubstituted or substituted,for example halo-substituted, C₁-C₄alkanecarboxylic acids, for exampleacetic acid, saturated or unsaturated dicarboxylic acids, for exampleoxalic, malonic, succinic, maleic, fumaric or phthalic acid,hydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaricor citric acid, or benzoic acid, or with organic sulfonic acids, such asunsubstituted or substituted, for example halo-substituted, C₁-C₄alkane-or aryl-sulfonic acids, for example methane- or p-toluene-sulfonic acid.Furthermore, compounds of formula (I) or (II) having at least one acidicgroup are capable of forming salts with bases. Suitable salts with basesare, for example, metal salts, such as alkali metal or alkaline earthmetal salts, for example sodium, potassium or magnesium salts, or saltswith ammonia or an organic amine, such as morpholine, piperidine,pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethyl-,diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- ortri-hydroxy-lower alkylamine, for example mono-, di- ortri-ethanolamine. In addition, corresponding internal salts may also beformed. Preference is given within the scope of the invention toagrochemically advantageous salts. In view of the close relationshipbetween the compounds of formula (I) and (II) in free form and in theform of their salts, any reference hereinbefore or hereinafter to thefree compounds of formula (I) and (II) or to their respective salts isto be understood as including also the corresponding salts or the freecompounds of formula (I) and (II), where appropriate and expedient. Thesame applies in the case of tautomers of compounds of formula (I) and(II) and the salts thereof. The free form is generally preferred in eachcase.

[0024] Preferred compounds of the formula (I) are those wherein

[0025] A is a pyrid-3-yl, 2-chloropyrid-5-yl,2-chloro-1-oxido-5-pyridinio or 2-chlorothiazol-5-yl group;

[0026] particularly a 2-chloropyrid-5-yl group or preferably a2-chlorothiazol-5-yl group;

[0027] wherein R is C₁-C₆alkyl, phenyl-C₁-C₄alkyl, C₃-C₄alkenyl orC₃-C₄alkynyl;

[0028] more especially C₁-C₄alkyl, preferably methyl;

[0029] R₁ and R₂ are independently of each other C₁-C₄-alkyl or benzyl,or together a group —CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—O—CH₂—, —CH₂—S—CH₂—,—CH₂—NH—CH₂—, —CH₂—N(CH₃)—CH₂—, especially group —CH₂—CH₂— or—CH₂—O—CH₂—, particularly —CH₂—O—CH₂—; and

[0030] X is N—NO₂ or N—CN, more especially N—NO₂.

[0031] Especially preferred is an at least quaternary pesticidalcomposition comprising an insecticidally effective amount of a compoundselected from the group consisting of: a compound of the formula

[0032] imidacloprid,(E)-1-(2-chlorothiazol-5-ylmethyl)-3-methyl-nitroguanidine (TI435),nitenpyram, thiacloprid, and acetamiprid; particularly the compound ofthe formula (Ia) (thiamethoxam).

[0033] The alkyl, alkoxy or acyl groups of the formula (II) arepreferably lower alkyl, alkoxy or acyl, that is to say radicals havingone to four carbon atoms.

[0034] A preferred group of insecticidally effective 1-arylpyrazoles(II) of the present invention are those wherein:

[0035] R₁ and R₂ are a halogen atom,

[0036] R₃ is 4-haloalkyl

[0037] R₄ is lower haloalkyl and R₅ is amino.

[0038] A specific 1-arylpyrazole (II) usable in the compositions andmethods falling within the scope of the present invention is fipronil.

[0039] The compounds of the formula (1) are known for instance fromEP-A-580 553;

[0040] Imidacloprid is known from The Pesticide Manual, 11th Ed. (1997),The British Crop Protection Council, London, page 706;

[0041] Nitenpyram from The Pesticide Manual, 11th Ed. (1997), TheBritish Crop Protection Council, London, page 880;

[0042] TI435 from EP-A-376,279;

[0043] Thiacloprid from EP-A-235,725; and

[0044] Fipronil from The Pesticide Manual, 11th Ed. (1997), The BritishCrop Protection Council, London, page 545.

Fungicide Components (B)

[0045] Preferred are at least quaternary pesticidal compositionscomprising as fungicidally active ingredient (B):

[0046] (B1) as first active ingredient at least one phenylamide(acylalanine type) of the formula (III):

[0047] wherein

[0048] R₁ is methyl; R₂ is in ortho position to the amino group and ismethyl, ethyl or chlorine; R₇ and R₈ independently are hydrogen ormethyl; R′ is methyl; and Y is —OR₄ or —SR₄ in which R₄ is methyl,ethyl, propyl, isopropyl, butyl, sec. butyl or tert. butyl; and

[0049] enantiomers thereof; in free from or in salt form.

[0050] Preferred phenylamide derivatives of formula (III) usable in thecompositions and methods falling within the scope of the presentinvention include metalaxyl; metalaxyl consisting of more than 70% byweight of the R-enantiomer; metalaxyl consisting of more than 85% byweight of the R-enantiomer; metalaxyl consisting of more than 92% byweight of the R-enantiomer; metalaxyl consisting of more than 97% byweight of the R-enantiomer; and mefenoxam (i.e., R-metalaxyl ormetalaxyl-M).

[0051] (B2) as second active ingredient at least one phenylpyrrole ofthe formula (IV):

[0052] wherein

[0053] X is hydrogen or CO—R₁, wherein R₁ is C₁-C₆alkyl which isunsubstituted or substituted by halogen or C₁-C₃alkoxy; or isC₃-C₆alkenyl, C₃-C₆alkynyl, or C₁-C₆alkoxy which is unsubstituted orsubstituted by halogen or C₁-C₃alkoxy; or is C₃-C₆alkenyloxy, orC₃-C₆cycloalkyl; in free from or in salt form.

[0054] A specific phenylpyrrole (IV) usable in the compositions andmethods falling within the scope of the present invention isfludioxonil.

[0055] (B3) As third active ingredient at least one triazole of theformula (V):

[0056] wherein

[0057] R₁₂, R₁₅ and R₁₈ are hydrogen, halogen, C₁-C₃alkyl, C₁-C₃alkoxyor nitro; in free from or in salt form.

[0058] A specific triazole (V) usable in the compositions and methodsfalling within the scope of the present invention is difenoconazole.

[0059] The compounds of the formula (III) are known for instance fromU.S. Pat. No. 4,151,299;

[0060] The compounds of the formula (IV) from U.S. Pat. No. 4,705,800;

[0061] The compounds of the formula (V) from U.S. Pat. No. 5,266,585;

[0062] Difenoconazole is known from The Pesticide Manual, 10th Ed.(1994), The British Crop Protection Council, London, page 328;

[0063] Fludioxonil from The Pesticide Manual, 11th Ed. (1997), TheBritish Crop Protection Council, London, page 566;

[0064] Metalaxyl from The Pesticide Manual, 11th Ed. (1997), The BritishCrop Protection Council, London, page 792; and

[0065] R-metalaxyl (mefenoxam) from The Pesticide Manual, 11th Ed.(1997), The British Crop Protection Council, London, page 794.

A.I. Combination

[0066] Surprisingly, it has been found that the combination of theactive ingredients (A), (B1), (B2) and (B3) results in a quiteunexpectedly enhanced action against insects or representatives of theorder Acarina and microorganisms such as seed-borne and soil-borne fungiand/or provides other unexpected advantages when used in connection withplant propagation materials. The increase in action and/or otheradvantageous properties achieved with the combination according to theinvention is significantly greater than the activity to be expected bythe four individual components, i.e. the activity is enhancedsynergistically which, inter alia, extends the boundaries of thepesticidal activity of the compounds.

[0067] In particular, it has now been found, surprisingly, that, forexample, the pesticidal activity of the compositions according to theinvention, compared with the pesticidal activity of the individualcomponents, is not merely additive, as may essentially be expected, butthat a synergistic effect exists. The term “synergistic” is not,however, in any way limited in this context to the pesticidal activity,but refers equally to other advantageous properties of the compositionsaccording to the invention as compared with the individual components.Examples of such advantageous properties that may be mentioned are: abroadening of the spectrum of pesticidal activity to other pests, forexample to resistant strains; a reduction in the rate of application ofthe active ingredients; adequate control of the pests with the aid ofthe compositions according to the invention, even at a rate ofapplication at which the individual compounds are totally ineffective;advantageous behavior during formulating and/or upon application, forexample upon grinding, sieving, emulsifying, dissolving or dispersing;increased storage stability; improved stability to light; moreadvantageous degradability; improved toxicological and/orecotoxicological behavior; improved crop characteristics including:emergence, crop yields, more developed root system, tillering increase,increase in plant height, bigger leaf blade, less dead basal leaves,stronger tillers, greener leaf color, less fertilizers needed, lessseeds needed, more productive tillers, earlier flowering, early grainmaturity, less plant verse (lodging), increased shoot growth, improvedplant vigor, and early germination; or any other advantages familiar toa person skilled in the art.

[0068] In the area of pest control, the compositions according to theinvention are valuable reductive (reducing the occurrence of a pest),preventive and/or curative active ingredients having a very advantageousbiocidal spectrum even at low rates of concentration, while being welltolerated by warm-blooded animals, fish and plants. The compositions ofthe invention are effective against all or individual development stagesof normally sensitive animal pests, but also of resistant animal pests,such as insects and representatives of the order Acarina, andphytopathogenic fungi. The insecticidal, acaricidal and/or fungicidalaction of the compositions of the invention may manifest itselfdirectly, i.e. in the mortality of the pests, which occurs immediatelyor only after some time, for example during molting, or indirectly, forexample in reduced oviposition and/or a reduced hatching rate, the goodactivity corresponding to a mortality of at least 50 to 60%.

[0069] Advantageous mixing ratios of the at least four activeingredients are (A):(B1):(B2):(B3)=(250 to 50):(5 to 1):(2 to 1):(20 to1), in particular (A):(B1):(B2):(B3)=(200 to 60):(3 to 1):(1.5 to 1):(10to 1) and very particularly (A):(B1):(B2):(B3)=(160 to 120):(3 to2):(1.2 to 1):(10 to 4). Other advantageous mixing ratios are(A):(B1):(B2):(B3)=(160):(3):(1):(9.6), or (120):(2):(1):(4.8).

[0070] The active ingredient combinations according to the inventionpreferably comprise a compound of formula (I) to (II), especially of theformula (I), more especially of the formula (Ia), and metalaxyl,fludioxonil and difenoconazole.

[0071] Preference is given especially to an active ingredientcombination comprising the compound of formula (Ia), metalaxyl-M,fludioxonil and difenoconazole in a mixing ratio of (160):(3):(1):(9.6)or (400 g):(7.5 g):(2.5 g):(24 g).

[0072] Other preferred ratios include: (200 g):(3.75 g):(1.25 g):(12 g)and (500 g):( 7.5 g):(2.5 g):(24 g).

[0073] The above-mentioned mixing ratios relate on the one hand to partsby weight of the individual components, but on the other hand also tothe mixing ratios in moles. Thus, for example, with respect to theprevious paragraph the ratio of (250 to 50):(1):(1):(1) denotes fromabout 250 to about fifty parts by weight of a compound of formula (Ia)to one part by weight of a each of metalaxyl-M, fludioxonil anddifenoconazole; but also from about 250 to about fifty moles of acompound of formula (Ia) to one mole of a each of the compoundsmetalaxyl-M, fludioxonil and difenoconazole. In addition, it will beunderstood that 1 part by weight may equal the actual weight of theactive component with the lowest loading. For example, a mixing ratio of(160):(3):(1):(9.6) parts would equal the ratio (400 g):(7.5 g):(2.5g):(24 g) in grams (wherein 2.5 grams is considered “1 part”). Finally,the figures relate also to mixtures in the ratio of the LD₅₀ values ofthe individual pests to be controlled.

[0074] In one embodiment, the application rate utlizing the above-notedmixing ratios is calculated per 100 kilograms of seed or other plantpropigation material to be treated.

Fungal Pests

[0075] The compositions according to the invention are especially activeagainst fungi, in particular of the oomycetes which belong to the classof phycomycetes (e.g., phytophthora, peronospora, pseudoperonospora,pythium sp. or plasmopara), basidiomycete, ascomycete, adelomycete orFungi Imperfecti type, such as Botrytis cinerea, Erysiphe graminis,Puccinia graminis, Puccinia recondita, Piricularia oryzae, Cercosoorabeticola, Puccinia striiformis, Erysiphe cichoracearum, Rhinchosporiumsecalis, Fusarium, Solani, Fusarium oxysporum (e.g. melonis),Pyrenophora avenae, Septoria tritici, Septoria avenae, Whetzeliniasclerotiorum, Mycosohaerella fijiensis, Alternaria solani, Aspergillusniger, Cercospora arachidicola, Cladosporium herbarum, Tilletia caries,Tilletia contreversa, Fusarium roseum, Fusarium nivale, Helminthosporiumoryzae, Helminthosporium teres, Helminthosporium gramineum,Helminthosporium sativum, Penicillium expansum, Pestalozzia sp, Phomabetae, Phoma foveata, Phoma lingam, Ustilago maydis, Ustilago nuda,Ustilago hordei, Ustilago avenae, Verticillium dahliae, Ascochyta pisi,Guignardia bidwellii, Corticium rolfsii, Phomposis viticola, Sclerotiniasclerotiorum, Sclerotinia minor, Coryneum cardinale, Rhizoctonia solani,Acrostalagmus koningi, Alternaria, Colletotrichum, Corticium rolfsii,Diplodia natalensis, Gaeumannomyces graminis, Gibberella fujikuroi,Hormodendron cladosporioides, Myrothecium verrucaria, Paecylomycesvarioti, Pellicularia sasakii, Phellinus megaloporus, Sclerotiumrolfsii, Stachybotris atra, Trichoderma pseudokoningi, Trichotheciumroseum.

[0076] The compositions according to the invention are particularlysuited for the reductive, preventive and the curative protection of theplant propagation material against fungi and fungal diseases including:damping off (e.g., Fusarium sp., Pythium sp., Rhizoctonia sp.), root rot(e.g., Pythium sp., Fusarium sp., Gibberella sp.), and seed or soilborne blackleg (Leptosphaeria maculans) diseases of vegetable organismsand plants in general, and especially of oil seed crops such as canola(rape), mustard seed, and hybrids thereof, and also rice and maize.

Insect Pests

[0077] The compositions according to the invention may be used for theprotection of the plant propagation material and developing plantsagainst animal pests such as insects and representatives of the orderAcarnia including:

[0078] from the order Lepidoptera, for example,

[0079] Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp.,Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp.,Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella,Carposina nipponensis, Chilo spp., Choristoneura spp., Clysiaambiguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp.,Coleophora spp., Crocidolomia binotalis, Cryptophlebia leucotreta, Cydiaspp., Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp.,Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp.,Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis,Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella,Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp.,Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp.,Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea,Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pierisspp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp.,Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp.,Tortrix spp., Trichoplusia ni and Yponomeuta spp.;

[0080] from the order Coleoptera, for example,

[0081] Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnematibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabroticaspp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata,Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchusspp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp-,Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Triboliumspp. and Trogoderma spp.;

[0082] from the order Orthoptera, for example,

[0083] Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaeamaderae, Locusta spp., Periplaneta spp. and Schistocerca spp.;

[0084] from the order Isoptera, for example,

[0085] Reticulitermes spp.;

[0086] from the order Psocoptera, for example,

[0087] Liposcelis spp.;

[0088] from the order Anoplura, for example,

[0089] Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigusspp. and Phylloxera spp.;

[0090] from the order Mallophaga, for example,

[0091] Damalinea spp. and Trichodectes spp.;

[0092] from the order Thysanoptera, for example,

[0093] Frankliniella spp., Hercinotnrips spp., Taeniothrips spp., Thripspalmi, Thrips tabaci and Scirtothrips aurantii;

[0094] from the order Heteroptera, for example,

[0095] Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistusspp., Eurygaster spp., Leptocorisa spp., Nezara spp., Piesma spp.,Rhodnius spp., Sahlbergella singularis, Scotinophara spp. and Tniatomaspp.;

[0096] from the order Homoptera, for example,

[0097]Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp.,Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplasterspp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccushesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp.,Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp.,Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp.,Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp.,Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotusspp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphisspp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae andUnaspis citri;

[0098] from the order Hymenoptera, for example,

[0099] Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae,Gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis,Neodiprion spp., Solenopsis spp. and Vespa spp.;

[0100] from the order Diptera, for example,

[0101] Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphoraerythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebraspp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilusspp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp.,Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseoliaspp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletispomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp. andTipula spp.;

[0102] from the order Siphonaptera, for example,

[0103] Ceratophyllus spp. und Xenopsylla cheopis and

[0104] from the order Thysanura, for example,

[0105] Lepisma saccharina.

[0106] The active ingredients according to the invention areparticularly suitable for controlling crucifer flea beetles (Phyllotretaspp.), root maggots (Delia spp.), cabbage seedpod weevil (Ceutorhynchusspp.) and aphids in oil seed crops such as canola (rape), mustard seed,and hybrids thereof, and also rice and maize.

Target Crops

[0107] Target crops within the scope of this invention are, for example,the following plant species: beet (sugar beet and fodder beet), oilplants (canola, rape, mustard seed, poppy, olives, sunflowers, coconut,castor oil plants, cocoa beans, groundnuts and soya). There also may bementioned peanuts, wheat sorghum and corn.

[0108] In addition, the crops listed in the crop group tables in 40 CFRSec. 180.41 (1995) are noted. 40 CFR Sec. 180.41 (1995) and the FederalRegister: May 17, 1995 (vol. 60, no. 95) pp. 26625-26643 are fullyincorporated by reference herein for their disclosure relating to usefulcrop plants:

[0109] (1) Crop Group 5: Brassica (Cole) Leafy Vegetables Group, forexample, broccoli, cauliflower; cabbage; and mustard greens;

[0110] (2) Crop Group 9: Cucurbit Vegetables Group, for example,cucumber, muskmelon and summer squash;

[0111] (3) Crop Group 11: Pome Fruits Group, for example, apple andpear;

[0112] (4) Crop Group 15: Cereal Grains Group, for example, corn andrice.

[0113] The following plants are to regarded as being particularlysuitable target crops for the at least quaternary pesticide compositionsof the invention: plant propagation materials (such as seeds) of oilplants (canola, rape, mustard seed, poppy, olives, sunflowers, coconut,castor oil plants, cocoa beans, groundnuts).

[0114] The seeds treated in accordance with the invention includeconventional as well as genetically enhanced or engineered varietiessuch as, for example, insect resistant (e.g., Bt.) as well as diseaseresistant varieties.

Seed Treatment

[0115] The at least quaternary pesticidal composition according to theinvention has proved especially advantageous for protecting seeds, inparticular, oil seeds such as canola. However, the inventive compositionis also suitable for direct treatment of the soil or of other parts ofthe plant. The inventive composition is well tolerated by plants, and isecologically acceptable.

[0116] The subject of the invention is also a method for protecting themultiplication products of plants (plant propagation materials) and theplants resulting therefrom against insects and fungal diseases, whereinthe said multiplication products are coated with an insecticidal andfungicidal and non-phytotoxic composition according to the invention.

[0117] The at least quaternary pesticidal composition according to theinvention is usually employed together with the adjuvants customary informulation technology. The combination of the active ingredients (A),(B1), (B2) and (B3) are normally applied to plant propagation materialin the form of compositions, but also can be applied to the seed or tothe locus of propagation thereof (such as a furrow), simultaneously orin succession, with further compounds. These further compounds can befertilizers or micronutrient donors or other preparations that influenceplant growth. They can also be selective herbicides, insecticides,fungicides, bactericides, insect growth regulators, plant growthregulators, nematicides, molluscicides or mixtures of several of thesepreparations, if desired, together with further carriers, surfactants orapplication-promoting adjuvants customarily employed in the art offormulation. In addition, there may be mentioned inoculants, brightenersand polymers.

[0118] This invention also includes suitable agricultural compositionsfor controlling insects and fungi on or in seed consisting essentiallyof at least quaternary pesticidal composition of this invention plus asuitable inert surfactant or an suitable inert liquid or a solidcarrier. As used herein, the phrase “consisting essentially of” does notexclude the presence of other active pesticidal materials orconventional formulating ingredients.

[0119] The active components (A), (B1), (B2) and (B3) are processed inknown manner to give, for example, emulsifiable concentrates,suspoemulsions, spreadable pastes, directly sprayable or dilutablesolutions, dilute emulsions, wettable powders, soluble powders, dusts,granules, and also for encapsulation in, for example, polymericsubstances. The application methods, such as spraying, misting,atomising, broadcasting, brushing or pouring, and the nature of thecomposition are adapted to suit the intended aims and the prevailingcircumstances. In general, favorable rates of application are 0.0005 tonot more than 0.5 kg, in particular 0.001-0.03 kg of each activeingredient (B1), (B2) and (B3) per 100 kg of material to be protected.With respect to the active ingredient (A), the favorable rates ofapplication can range from 0.005 to not more than 1 kg, in particular0.01-0.8 kg, more particularly 0.1-0.5 kg per 100 kg of material to beprotected. However, the application conditions depend essentially on thenature (surface area, consistency, moisture content) of the material andon its environmental factors. Accordingly, within these ranges, thoseskilled in the art will choose, on the basis of their general body ofknowledge and, where appropriate, a few experiments, doses which arenon-phytotoxic but effective from a fungicidal and/or insecticidalstandpoint.

[0120] The term “plant propagation material” is understood to denote althe generative parts of the plant such as seeds which can be used forthe multiplication of the latter and vegetative plant material such ascuttings and tubers (for example potatoes). There may be mentioned,e.g., the seeds (in the strict sense), roots, fruits, tubers, bulbs,rhizomes, parts of plants. Germinated plants and young plants which areto be transplanted after germination or after emergence from the soil,may also be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion.

[0121] Also within the scope of the present invention, storage goodswhich can be protected with the mixture according to the invention, inparticular plant propagation material, especially seeds, will beunderstood as meaning natural substances of vegetable and/or animalorigin and their processing products for which long-term protection isdesired, for example the plants and parts thereof, which are mentionedbelow (stalks, leaves, tubers, seeds, fruits, grains) which have beentaken from the natural life cycle and which exist in the freshlyharvested state or in processed form (pre-dried, moistened, comminuted,ground, pressed, roasted, etc.). Also falling within the scope of theinvention is the protection of timber, whether in the form of crudetimber (construction timber, electricity pylons, barriers) or in theform of finished articles (furniture, objects made from wood). Naturalproducts of animal origin which are to be preserved, for example hides,furs, hairs and the like, likewise fall within the scope of theinvention.

[0122] The techniques of seed treatment application are well known tothose skilled in the art, and they may be used readily in the context ofthe present invention. The active ingredients can be formulated andapplied as a slurry, a solid seed coating, a soak, or as a dust on thesurface of the seed. There also may be mentioned, e.g., film-coating orencapsulation. The coating processes are well known in the art, andemploy, for seeds, the techniques of film-coating or encapsulation, orfor the other multiplication products, the techniques of immersion.Needless to say, the method of application of the compounds to the seedmay be varied and the invention is intended to include any techniquewhich is to be used.

[0123] A preferred method of applying the mixture according to theinvention consists in spraying or wetting the plant propagation materialwith a liquid preparation, or mixing the plant material with a solidpreparation of the active ingredients.

[0124] The compounds of this invention may be formulated or mixed in theseed treater tank or combined on the seed by overcoating with other seedtreating agents. The agents to be mixed with the compounds of thisinvention may be for the control of pests, modification of growth,nutrition, or for the control of plant diseases.

Formulations

[0125] The formulations, i.e. the compositions, preparations orcombinations containing the active ingredients (A), (B1), (B2) and (B3),as well as, if appropriate, suitable inert solid or liquid carriers, areprepared in a known manner, for example by intimately mixing and/orgrinding the active ingredients with inert, agriculturally-acceptableextenders, for example with solid or liquid carriers and, ifappropriate, surface-active compounds (surfactants). Such compositionsmay be advantageously formulated as flowable compositions, suspensions,microsuspensions, suspoemulsions, wettable powders, granulatedconcentrates, microemulsions and the like, all of which lend themselvesto seed treatment application and provide the requisite plantprotection.

[0126] The term “carrier” in the present description denotes a naturalor synthetic, organic or inorganic material with which the activesubstance is combined in order to facilitate its application to theplant, to the seeds or to the soil. This carrier is hence generallyinert, and it must be agriculturally acceptable, in particular to theplant being treated. The carrier may be solid (clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilizers, and thelike) or liquid (water, alcohols, ketones, petroleum fractions, aromaticor paraffinic hydrocarbons, chlorinated hydrocarbons, liquefied gases,and the like).

[0127] Suitable liquid carriers are: aromatic hydrocarbons, inparticular the fractions C₈ to C₁₂, such as xylene mixtures orsubstituted naphthalenes, phthalic esters such as dibutly or dioctylphthalate, aliphatic hydrocarbons such as cyclohexane or paraffins,alcohols and glycols as well as their ethers and esters, such asethylene glycol monomethyl ether, ketones such as cyclohexanone,strongly polar solvents such as N-methyl-2-pyrrolidone, dimethylsulfoxide or dimethylformamide, and, if appropriate, epoxidizedvegetable oils or soybean oil; or water.

[0128] Solid carriers which may be used, for example for dusts anddispersible powders, are calcite, talc, kaolin, montmorillonite orattapulgite, highly-disperse silica or absorptive polymers. Possibleparticulate, adsorptive carriers for granules are pumice, crushed brick,sepiolite or bentonite, montmorillonite-type clay, and possiblenonsorbent carrier materials are calcite or dolomite.

[0129] Suitable surface-active compounds are non-ionic, cationic and/oranionic surfactants having good emulsifying, dispersing and wettingproperties, depending on the nature of the active ingredients (A), (B1),(B2) and (B3) to be formulated. Surfactants will also be understood asmeaning mixtures of surfactants.

[0130] The surfactants customarily employed in formulation technologyare described, inter alia, in the following publications:

[0131] “McCutcheon's Detergents and Emulsifiers Annual”, MC PublishingCorp., Glen Rock, N.J., 1988.

[0132] M. and J. Ash, “Encyclopedia of Surfactants”, Vol. I-III,Chemical Publishing Co., New York, 1980-1981.

[0133] Among the suitable surfactants there may be mentioned, e.g.,polyacrylic acid salts, lignosulphonic acid salts, phenolsulphonic or(mono- or di-alkyl)naphthalenesulphonic acid salts, laurylsulfate salts,polycondensates of ethylene oxide with lignosulphonic acid salts,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, substituted phenols (in particularalkylphenols or arylphenols such as mono- and di-(polyoxyalkylenealkylphenol) phosphates, polyoxyalkylene alkylphenol carboxylates orpolyoxyalkylene alkylphenol sulfates), salts of sulphosuccinic acidesters, taurine derivatives (in particular alkyltaurides),polycondensates of ethylene oxide with phosphated tristyrylphenols andpolycondensates of ethylene oxide with phosphoric esters of alcohols orphenols. The presence of at least one surfactant is often requiredbecause the active substance and/or the inert vehicle are not soluble inwater and the carrier agent for the application is water.

[0134] Furthermore, particularly useful adjuvants which enhanceapplication are natural or synthetic phospholipids from the series ofthe cephalins and lecithins, for example phosphatidylethanolamine,phosphatidylserine, phosphatidylglycerine or lysolecithin.

[0135] The agrochemical compositions generally contain: 0.1 to 99%, inparticular 9 to 50%, more particularly 20 to 25% of the activesubstances (A), (B1), (B2) and (B3); the balance of the formulationcomprising a solid and/or liquid carrier along with optionalsurfactant(s) and other optional inert ingredients known in the art suchas, e.g., protective colloids, adhesives, thickeners, thixotropicagents, penetrating agents, preservatives, stabilizers, antifoamingagents, antifreeze agents, sequestering agents, dyes, pigments,colorings and polymers.

[0136] In one embodiment, commercial products will preferably beformulated as concentrates whereas the end user will normally use diluteformulations.

Formulation Examples (%=percent by weight)

[0137] The examples which follow are intended to illustrate and notlimit the invention, “active ingredient” being understood as meaning amixture of the active substances (A), (B1), (B2) and (B3) in aparticular mixing ratio of (A):(B1):(B2):(B3)=(160 to 120):(3 to 2):(1.2to 1):(10 to 4). Example F1: Emulsifiable concentrates a) b) c) activeingredients 25% 40% 50% calcium dodecylbenzenesulfonate  5%  8%  6%castor oil polyethylene glycol ether  5% — — tributylphenol polyethyleneglycol ether — 12%  4% cyclohexanone — 15% 20% xylene mixture 65% 25%20% Emulsions of any desired concentration can be prepared from thisconcentrate by dilution with water, and can be employed in cropprotection and in seed treatment applications. Example F2: Dusts a) b)active ingredients  5%  8% talc 95% — kaolin — 92% Ready-to-use dustsare obtained by mixing the active ingredients with the carrier andgrinding the mixture in a suitable mill. Such powders can be used fordry-dressing seeds. Example F3: Wettable powders a) b) c) activeingredients 25% 50% 75% sodium lignosulfonate  5%  5% — sodiumlaurylsulfate  3% —  5% sodium diisobutylnaphthalenesulfonate —  6% 10%octylphenol polyethylene glycol ether —  2% — highly dispersed silicicacid  5% 10% 10% kaolin 62% 27% — The active ingredient is mixedthoroughly with the additives and the mixture is ground thoroughly in asuitable mill affording wettable powders which can be diluted with waterto give suspensions of any desired concentration. Such slurries can beused for carrying out furrow treatments on prior to planting crops ofplants and also for wet- or moist-dressing material which can bepropagated, for example oil seeds or tubers of plants. Example F4:Suspoemulsions a) active ingredients 22.5% sulfated nonylphenol(polyoxyethylene condensate)  0.1% phosphated tristyrylphenol(polyoxyethylene condensate)   4% sodium lignosulfonate (polyoxyethylenecondensate)   2% NaOH (50%)  0.1% silicone defoaming agent  0.1%pigment(s)  9.5% glycerin   20% xanthan gum  0.2% water 41.5%

[0138] This formulation is suitable for mixtures of solid and liquidactive ingredients. The solid active ingredient(s) are mixed thoroughlywith a portion of the emulsifiers and water and the mixture is groundthoroughly in a suitable mill. Another portion of the emulsifiers andwater are mixed with the liquid active ingredient(s). The two mixturesare combined along with any other inert ingredients (such as pigments,thickeners, etc.) that are to be used in the formulation. Suchsuspoemulsions can be used for carrying out in furrow treatments priorto planting crops of plants and also for wet- or moist-dressing materialwhich can be propagated, for example oil seeds or tubers of plants.

Biological Examples

[0139] Biological Examples (%=percent by weight unless otherwiseindicated)

[0140] The examples which follow are intended to illustrate and notlimit the invention. The pesticidal composition of the invention used inthe examples comprises the following active ingredient (a.i.) mixtureused at the noted application rate: Application Rate Active IngredientMixture (grams a.i./ 100 kg seed) (A)  Thiamethoxam 400 (B1) Mefenoxam7.5 (B2) fludioxonil 2.5 (B3) difenconazole 24

Example B1: Emergence

[0141] Canola seed is treated with the pesticidal composition of theinvention the rates given above and is seeded following procedures whichcorrespond to conditions found in practice. Untreated seeds from thesame origin are used for comparison purposes. Emergence (plants permeter) is evaluated. TABLE B1 Treated Seed Untreated Seed 23 plants/m 18plants/m

Example B2: Vigor

[0142] Canola seed is treated with the pesticidal composition of theinvention at the rates given above and is seeded following procedureswhich correspond to conditions found in practice under high cruciferflea beetle pressure. Untreated seeds from the same origin are used forcomparison purposes. Plant vigor (1-2 leaf stage) is evaluated. TABLE B2Treated Seed Untreated Seed 94% 18%

Example B3: Yields

[0143] Canola seed is treated with the pesticidal composition of theinvention at the rates given above and is seeded following procedureswhich correspond to conditions found in practice. The crop is harvestedfrom the field at maturity. Untreated seeds from the same origin areused for comparison purposes. Crop yield (bushels per acre) isevaluated. TABLE B3 Treated Seed Untreated Seed 43 (bu/ac) 28 (bu/ac)

[0144] In summary, it is seen that this invention provides a new atleast quaternary pesticidal composition for the protection of plantpropagation materials. Variations may be made in proportions, proceduresand materials without departing from the scope of the invention asdefined by the following claims.

We claim:
 1. An at least quaternary pesticide composition comprising asactive ingredients: (A) an insecticidally or acaricidally effectiveamount of a compound of the formulae (I) or (II)

wherein A is 2-chloropyrid-5-yl, 2-methylpyrid-5-yl,1-oxido-3-pyridinio, 2-chloro-1-oxido-5-pyridinio,2,3-dichloro-1-oxido-5-pyridinio, tetrahydrofuran-3-yl,5-methyl-tetrahydrofuran-3-yl or 2-chlorothiazol-5-yl group, R ishydrogen, C₁-C₆alkyl, phenyl-C₁-C₄alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenylor C₂-C₆alkynyl; R₁ and R₂ are independently of each other C₁-C₄-alkyl,C₁-C₄-alkenyl, C₁-C₄-alkinyl, —C(═O)—CH₃ or benzyl; or together form agroup —CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—O—CH₂—, —CH₂—S—CH₂—, —CH₂—NH—CH₂—or —CH₂—N(CH₃)—CH₂—; and X is N—NO₂ or N—CN or CH—NO₂; , or, whereappropriate, a tautomer thereof, in each case in free from or in saltform; or at least one phenylpyrazole compound of formula (II)

wherein R₁ and R₂ may represent a hydrogen or halogen atom (at least oneof them is preferably other than hydrogen), R₃ may represent a halogenatom or a haloalkyl or haloalkoxy or SF₅ group, in the 4 position on thephenyl ring, R₄ may represent an alkyl or haloalkyl group, R₅ mayrepresent an amino group which may be mono- or di- substituted by analkyl or haloalkyl radical, acyl, alkoxycarbonyl, and n is 0, 1 or 2; infree from or in salt form; and (B) a fungicidally effective amount of atleast three fungicides selected from the group consisting of formulae(III), (IV) and (V):

wherein R₁ is methyl; R₂ is in ortho position to the amino group and ismethyl, ethyl or chlorine; R₇ and R₈ independently are hydrogen ormethyl; R′ is methyl; and Y is —OR₄ or —SR₄ in which R₄ is methyl,ethyl, propyl, isopropyl, butyl, sec. butyl or tert. butyl; andenantiomers thereof, in free from or in salt form;

wherein X is hydrogen or CO—R₁, wherein R₁ is C₁-C₆alkyl which isunsubstituted or substituted by halogen or C₁-C₃alkoxy; or isC₃-C₆alkenyl, C₃-C₆alkynyl, or C₁-C₆alkoxy which is unsubstituted orsubstituted by halogen or C₁-C₃alkoxy; or is C₃-C₆alkenyloxy, orC₃-C₆cycloalkyl; in free from or in salt form; and

wherein R₁₂, R₁₅ and R₁₈ are hydrogen, halogen, C₁-C₃alkyl, C₁-C₃alkoxyor nitro; in free from or in salt form; together with a suitable carriertherefor.
 2. A composition according to claim 1 which contains (A) aninsecticidally or acaricidally effective amount of a compound selectedfrom the group consisting of: a compound of the formula

(Ia), imidacloprid,(E)-1-(2-chlorothiazol-5-ylmethyl)-3-methyl-nitroguanidine (TI435),nitenpyram, thiacloprid, and acetamiprid.
 3. A composition according toclaim 2 which contains (A) an insecticidally or acaricidally effectiveamount of a compound of the formula

(Ia).
 4. A composition according to claim 1 which contains (A) aninsecticidally or acaricidally effective amount of fipronil.
 5. Acomposition according to claim 1 which contains (B1) a fungicidallyeffective amount of a compound selected from the group consisting ofmetalaxyl; metalaxyl consisting of more than 70% by weight of theR-enantiomer; metalaxyl consisting of more than 85% by weight of theR-enantiomer; metalaxyl consisting of more than 92% by weight of theR-enantiomer; metalaxyl consisting of more than 97% by weight of theR-enantiomer; and mefenoxam.
 6. A composition according to claim 1 whichcontains (B2) a fungicidally effective amount of fludioxonil.
 7. Acomposition according to claim 1 which contains (B3) a fungicidallyeffective amount of difenoconazole.
 8. A composition according to claim1 which contains: (A) an insecticidally or acaricidally effective amountof a compound of the formula

(B) a fungicidally effective amount of of at least three fungicidesselected from the group consisting of (B1) mefenoxam, (B2) fludioxoniland (B3) difenoconazole.
 9. A composition according to claim 8 whereinthe ratio of active ingredients (A):(B1):(B2):(B3) is (400 g):(7.5g):(2.5 g):(24 g).
 10. Pest-resistant plant propagation materialcomprising plant propagation material treated with a pesticidallyeffective amount of a pesticidal composition, wherein said pesticidalcomposition comprises as active ingredients: (A) an insecticidally oracaricidally effective amount of a compound of the formulae (I) or (II)

wherein A is 2-chloropyrid-5-yl, 2-methylpyrid-5-yl,1-oxido-3-pyridinio, 2-chloro-1-oxido-5-pyridinio,2,3-dichloro-1-oxido-5-pyridinio, tetrahydrofuran-3-yl,5-methyl-tetrahydrofuran-3-yl or 2-chlorothiazol-5-yl group, R ishydrogen, C₁-C₆alkyl, phenyl-C₁-C₄alkyl, C₃-C₆cycloalkyl, C₂-C₆alkenylor C₂-C₆alkynyl; R₁ and R₂ are independently of each other C₁-C₄-alkyl,C₁-C₄-alkenyl, C₁-C₄-alkinyl, —C(═O)—CH₃ or benzyl; or together form agroup —CH₂—CH₂—, —CH₂—CH₂—CH₂—, —CH₂—O—CH₂—, —CH₂—S—CH₂—, —CH₂—NH—CH₂—or —CH₂—N(CH₃)—CH₂—; and X is N—NO₂ or N—CN or CH—NO₂;, or, whereappropriate, a tautomer thereof, in each case in free from or in saltform; or at least one phenylpyrazole compound of formula (II)

wherein R₁ and R₂ may represent a hydrogen or halogen atom (at least oneof them is preferably other than hydrogen), R₃ may represent a halogenatom or a haloalkyl or haloalkoxy or SF₅ group, in the 4 position on thephenyl ring, R₄ may represent an alkyl or haloalkyl group, R₅ mayrepresent an amino group which may be mono- or di- substituted by analkyl or haloalkyl radical, acyl, alkoxycarbonyl, and n is 0, 1 or 2; infree from or in salt form; and (B) a fungicidally effective amount of atleast three fungicides selected from the group consisting of formulae(III), (IV) and (V):

wherein R₁ is methyl; R₂ is in ortho position to the amino group and ismethyl, ethyl or chlorine; R₇ and R₈ independently are hydrogen ormethyl; R′ is methyl; and Y is —OR₄ or —SR₄ in which R₄ is methyl,ethyl, propyl, isopropyl, butyl, sec. butyl or tert. butyl; andenantiomers thereof, in free from or in salt form;

wherein X is hydrogen or CO—R₁, wherein R₁ is C₁-C₆alkyl which isunsubstituted or substituted by halogen or C₁-C₃alkoxy; or isC₃-C₆alkenyl, C₃-C₆alkynyl, or C₁-C₆alkoxy which is unsubstituted orsubstituted by halogen or C₁-C₃alkoxy; or is C₃-C₆alkenyloxy, orC₃-C₆cycloalkyl; in free from or in salt form; and

wherein R₁₂, R₁₅ and R₁₈ are hydrogen, halogen, C₁-C₃alkyl, C₁-C₃alkoxyor nitro; in free from or in salt form; together with a suitable carriertherefor.
 11. A pest-resistant plant propagation material according toclaim 10 wherein said pesticidal composition contains (A) aninsecticidally or acaricidally effective amount of a compound selectedfrom the group consisting of: a compound of the formula

(Ia), imidacloprid,(E)-1-(2-chlorothiazol-5-ylmethyl)-3-methyl-nitroguanidine (TI-435),nitenpyram, thiacloprid, and acetamiprid.
 12. A pest-resistant plantpropagation material according to claim 11 wherein said pesticidalcomposition contains (A) an insecticidally or acaricidally effectiveamount of a compound of the formula

(Ia).
 13. A pest-resistant plant propagation material according to claim10 wherein said pesticidal composition contains (A) an insecticidally oracaricidally effective amount of fipronil.
 14. A pest-resistant plantpropagation material according to claim 10 wherein said pesticidalcomposition contains (B1) a fungicidally effective amount of a compoundselected from the group consisting of metalaxyl; metalaxyl consisting ofmore than 70% by weight of the R-enantiomer; metalaxyl consisting ofmore than 85% by weight of the R-enantiomer; metalaxyl consisting ofmore than 92% by weight of the R-enantiomer; metalaxyl consisting ofmore than 97% by weight of the R-enantiomer; and mefenoxam.
 15. Apest-resistant plant propagation material according to claim 10 whereinsaid pesticidal composition contains (B2) a fungicidally effectiveamount of fludioxonil.
 16. A pest-resistant plant propagation materialaccording to claim 10 wherein said pesticidal composition contains (B33)a fungicidally effective amount of difenoconazole.
 17. A pest-resistantplant propagation material according to claim 10 wherein said pesticidalcomposition contains: (A) an insecticidally or acaricidally effectiveamount of a compound of the formula

(Ia); and (B) a fungicidally effective amount of of at least threefungicides selected from the group consisting of (B1) mefenoxam, (B2)fludioxonil and (B3) difenoconazole.
 18. A pest-resistant plantpropagation material according to claim 17 wherein the ratio of activeingredients (A):(B1):(B2):(B3) in said pesticidal composition is (400g):(7.5 g):(2.5 g):(24 g).
 19. A method of protecting plant propagationmaterial against against attack by insects or representatives of theorder order Acarina and phytopathogenic fungi which comprises treatingsaid plant propagation material with an insecticidally (or acaricidally)and fungicidally effective amount of a composition according to claim 1.20. A method according to claim 19 wherein said plant propagationmaterial is a plant seed selected from the group consisting of canola,rape, mustard seed, poppy, olives, sunflowers, coconut, castor oilplants, cocoa beans, groundnuts.